Oxidation of cis‐ and trans‐3,5‐Di‐tert‐butyl‐3,5‐diphenyl‐1,2,4‐trithiolanes: Isolation and Properties of the 1‐Oxides and the 1,2‐Dioxides.

doi:10.1002/CHIN.200429129

Paper

Oxidation of cis‐ and trans‐3,5‐Di‐tert‐butyl‐3,5‐diphenyl‐1,2,4‐trithiolanes: Isolation and Properties of the 1‐Oxides and the 1,2‐Dioxides.

Published Jul 20, 2004 · H. Oshida, A. Ishii, J. Nakayama

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Abstract

Oxidation of trans-3,5-di-tert-butyl-3,5-diphenyl-1,2,4-trithiolane with dimethyldioxirane (DMD) or m-chloroperbenzoic acid (MCPBA) gave two stereoisomeric (1S*,3S*,5S*)- and (1R*,3S*,5S*)-1-oxides (16 and 17, respectively). Oxidation of 16 with DMD gave the (1S*,2R*,3S*,5S*)-1,2-dioxide (18) and the 1,1-dioxide 19, and that of 17 yielded the (1R*,2R*,3S*,5S*)-1,2-dioxide (20) mainly along with 18 and 19. The structures of the 1,2-dioxides 18 and 20 were determined by X-ray crystallography. 1,2-Dioxides 18 and 20 isomerized to each other in solution, and the equilibrium constant K (20/18) is 19 in CDCl3 at 295 K. The kinetic study suggested a biradical mechanism for the isomerization. Isomerization of 16 and 17 to cis-3,5-di-tert-butyl-1,2,4-trithiolane 1-oxides by treatment with Me3O+BF4- is also described.

Study Snapshot

Oxidation of trans-3,5-di-tert-butyl-3,5-diphenyl-1,2,4-trithiolane with dimethyldioxirane or m-chloroperbenzoic acid yields two stereoisomeric 1,2-dioxides

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Oxidation of cis‐ and trans‐3,5‐Di‐tert‐butyl‐3,5‐diphenyl‐1,2,4‐trithiolanes: Isolation and Properties of the 1‐Oxides and the 1,2‐Dioxides.

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